The pupil confronted his master inside his old classroom as Robbie Neilson's Dundee United side held Craig Levein's Hearts to a 1-1 draw at Tynecastle Park.
The Edinburgh club earned a bonus point in this opening Betfred Cup Group A tie thanks to a 5-3 penalty shootout win.
Neilson's Championship side produced a gutsy display and were anything but overawed against Premiership opposition. The head coach was returning to the club where he played and managed for almost 13 years and would have enjoyed seeing his team mix it with a top-six Scottish club.
Recent signing Lawrence Shankland scored nine minutes into his United debut, with Hearts restoring parity through 19-year-old youth graduate Andy Irving's first goal in maroon near half-time. Irving was sent off on 84 minutes for handling and denying Nicky Clark a clear scoring opportunity, but Hearts prevailed when the tie went to penalties.
They granted a second debut to Jamie Walker and a competitive debut to Conor Washington in front of the BT Sport cameras. Their third summer signing, Craig Halkett, started as a substitute with Sean Clare and Irving given opportunities in central midfield. United were without the former Tynecastle striker Osman Sow through a calf complaint but Shankland made his debut at centre-forward.
Chants of “Robbie Neilson's Tangerine Army” emanated from the away support as United started purposefully, culminating in a ninth-minute breakthrough. Christophe Berra's clearance landed at Sam Stanton's feet for a sharp one-two with Clark. Stanton then drove into the Hearts penalty area and crossed for Shankland to plant a downward header into the net - with goalkeeper Zdenek Zlamal out of position beyond his front post expecting a shot. Neilson spun away with a roar of jubilation in the technical area.
Hearts reacted with Washington shooting wide before the United goalkeeper Benjamin Siegrist stopped Jake Mulraney's effort. Walker then sprinted on to Uche Ikpeazu's inch-perfect pass to face Siegrist one-on-one, but the Swiss was again equal to the task. The visitors were now playing on the break in a fast-paced encounter, aided by a slick surface due to torrential rain in Gorgie.
Washington headed Hearts' clearest scoring opportunity of the first half over the crossbar from Mulraney's 30th-minute cross. Although the hosts were fashioning chances, they were toiling to convert. Irving remedied that as the interval approached.
Clare's tame free-kick from the right was prodded out by Stanton and dropped to the young midfielder 20 yards from goal. He returned it first time with a left-footed volley which whistled past Siegrist and into the keeper's bottom left corner. He looked delighted at doing so knowing it aided his claim for game time this season.
Pressure from Hearts continued after the break, with Ikpeazu forcing Siegrist down to his left for a save near the hour mark. Wide areas were bringing Levein's side joy as Walker and Mulraney were assisted by attacking full-backs Michael Smith and Aaron Hickey respectively.
Yet United were holding their own against opponents from a division above as the game entered its last 20 minutes. They remained perfectly happy with the scoreline at 1-1.
Another volley from Irving rolled narrowly past the post and Siegrist collected Smith's shot. Then came the Tayside side's priceless chance for a winner. Liam Smith's cross found substitute Louis Appere, whose effort was smothered and landed at Clark's feet. His attempted lob was deflected away for a corner with Zlamal spreading himself and the goal gaping.
Substitute Dario Zanatta's head flick following a corner almost crept in at the far post before Hearts were reduced to ten men. Irving chased a long ball towards his own goal but slipped on the sodden turf and handled on the ground with Clark ready to pounce. He received a straight red card.
The final whistled signalled penalties. Hearts scored all five through Clare, Oliver Bozanic, Smith, Washington and John Souttar. Clark's effort was saved by Zlamal and although Paul McMullan, Scott Banks and Bouhenna all converted, the hosts collected the bonus point.
Hearts (4-4-2): Zlamal; M Smith, Souttar, Berra, Hickey; Walker (McDonald 80), Clare, Irving, Mulraney (Zanatta 75); Ikpeazu (Bozanic 84), Washington. Unused subs: Doyle, Halkett, Burns, Edwards.
Dundee Utd (4-2-3-1): Siegrist; L Smith, Connolly, Reynolds, Sporle (Butcher 46); Bouhenna, Stanton (Banks 73); McMullan, Clark, Robson; Shankland (Appere 63). Unused subs: Deniz, C Smith, Harkes, King.
Referee: Kevin Clancy.